Cellulose organic derivative compositions containing glycol tetrahydrofuroates



Patented Jan. 9 1940 UNITED STATES oE-LLULosr; ORGANIC DERIVATIVE '00M- 7 POSITIONS CONTAINING GLYCOL'TETRA- 'nYDRoFUnoAr s Joseph B. Dickey and James B.- Normington,

Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey Ne Drawing. Application April a Serial No. 265,550.

screams. (o1. 106--40) p I tetrahydrofuroate, butyl ether of diethylene This invention relates to compositionsof matter in which cellulose organic derivatives, such as Y analogous arts, such, for instance, as the manu I facture of wrapping sheets or tissue, photographic our cellulose ethers, by adding thereto as a plasfilm, molding compounds and products, artificial silk, varnishes or lacquers, coating compositions,-

interlayers for laminated glass, and the like.

Oneobject of this invention is to produce compositions of matter which may be made into permanently transparent, strong and flexible sheets or films of desired thinness which are substantially waterproof, are unaffected by ordinary produce compositions of matter which are capable of easy and convenient manipulation in the plastic and analogous arts, such as in the manufacture of sheets, film, artificial silk filaments, varnishes, lacquers and the like, and to produce compositions which will not injure, or be injured by, the substances or surfaces with which they are associated during manufacture. Another object of our invention is to produce compositions which can be molded at elevated temperatures and high pressures to produce plastic products having the desirable properties of hardness, toughness and elasticity. Still another object of invention is to produce interlayers, for laminated glass which retain their properties of toughness and elasticity at low temperatures. Other objects will become apparent to those skilled in the artto which this invention pertains. y

We have discovered that valuable properties may be induced in and/or contributed to come. positions containing organic derivatives of cellulose, such as cellulose organic acid esters: and.

ticizing compound, a. neutral tetrahydrofuroate of a compound of the class consisting of glycols and glycol monoalkyl ethers. These tetrahydrofuroates are claimed in the co-pending' application' of Joseph B. Dickey and James G. McNally,

Serial No. 247,094, filed .December 21, 1938.,

Among these tetrahydrofuroates there may be mentioned, by way of examples, butoxyethyl glycol di-tetrah ydrofuroate,.ethylether of diethylene glycol tetrahydrofuroate, ethylene glycol di-tetrahydrofuroate, triethylene glycol di-tetrahydrofuroate, and trimethyleneglycol di tetrahydrofuroate. The particularly useful properties I ture in 300 to 500 parts, preferably 400 parts, by

weight, of acetone. To this solution may be added from 10 to 50'parts by weight of a neutral tetrahydrofuroate of a glycol or glycol ether. Within the limits stated, the amount of plas ticizer may be decreased or increased, depending upon whether it is desired to decrease or increase, respectively, the properties which this plasticizer contributes to the'finished product. The amount of solvent employed may also be increased or decreased, depending upon whether it is desired to have a more or less freely flowing composition, respectively.

A composition of matter prepared as above described may be deposited upon any suitable filmforming surface and the acetone evaporated therefrom to form a film or sheet, in a manner Well known to those skilled in the art. A film so produced has permanently brilliant transparency and lowinfiammab-ility, burning nomore readily than ordinaryv newsprint. Films or sheets produced in accordance with ourinventionare very tough and flexible, and maintain flexibility in a superior fashion, even at a temperature of -l0 F.

Other volatile solvents which are compatible with the cellulose acetate and our new plasticizers will also occur to those skilledin this art, such as ethylene chloride-alcohol mixtures, ethylene chloride-dioxan, mixtures, etc. .In like manner these plasticizers may be compoundedwith other single organic acid esters of cellulose, such as tate-lactate, cellulose acetate-tartrate and the like, or with cellulose ethers, such for instance, as ethyl cellulose and benzyl cellulose, a suitable solvent which will dissolve both the cellulosic derivative and the plasticizer being employed: for example, an alkylene chloride with or without the addition of an alcohol, or one of the many known volatile solvents for cellulose ethers. For instance, cellulose acetate-propionate and one of our novel tetrahydrofuroate plasticizers may be dissolved in ethylene chloride or in a mixture of propylene chloride and methanol, and sheets of excellent flexibility may be deposited from these solutions. Other substances, such as fire-retardents, evaporation retardants, etc., may be added to the film-forming compositions.

Our novel tetrahydrofuroate plasticizers may also be advantageously used as plasticizers in cellulose organic derivative molding compositions. For instance, from to 150 parts of the plasticizer, depending on the hardness or softness of the plastic desired, may be homogeneously mixed With cellulose acetate, and the mixture converted into a transparent plastic product by molding at a temperature of ll0160 C. and a pressure of 2500 to 4000 pounds per square inch for a period of from 2 to 5 minutes, in a manner well known to those skilled in molding compounds of that nature. The softer plastics may be extruded through a die. Interlayers for laminated glass may be deposited from a solvent or formed by extrusion with or without the use of a volatile solvent.

What we claim as our invention and desire to be secured by Letters Patent of the United States 1. A composition of matter comprising a cellulose organic derivative and, as a plasticizer therefor, a neutral tetrahydrofuroate of a compound of the class consisting of glycols and glycol monoalkyl ethers.

2. A transparent, flexible sheet comprising parts by weight of a cellulose organic derivative and, as a plasticizertherefor, from 5 to parts by weight, approximately, of a neutral tetrahydrofuroate of a compound of the class consisting of glycols and glycol monoalkyl ethers.

3. A composition of matter comprising a cellulose organic derivative and butoxyethyl tetrahydrofuroate as a plasticizer therefor.

4. A composition'of matter comprising a cellulose organic derivative and the ethyl ether of diethylene glycol tetrahydrofuroate as a plasticizer therefor.

5. A composition of matter comprising a cellulose organic derivative and trimethylene glycol di-tetrahydrofuroate as a plasticizer therefor.

6. A transparent, flexible sheet comprising 100 parts by weight of. a cellulose organic derivative and from 5 to 150 parts by weight, approximately, of butoxyethyl tetrahydrofuroate as a plasticizer therefor.

'7. A transparent, flexible sheet comprising 100 parts by Weight of a cellulose organic derivative and from 5 to 150 parts by weight, approximately, of the ethyl ether of diethylene glycol tetrahydrofuroate as a plasticizer therefor.

8. A transparent, flexible sheet comprising 100 parts by weight of a cellulose organic derivative and from 5 to 150 parts by weight, approximately, of trimethylene glycol di-tetrahydrofuroate as a plasticizer therefor.

JOSEPH B. DICKEY. JAMES B. NORMINGTON. 

